So while your analysis is correct and the cancellation rate will likely rise over time, the key thing to check when comparing a pre-change cohort to a post-change cohort to test for improvement is that the cancellation rates at two weeks post-signup are significantly different. Obviously its the most ideal if you can run the tests in parallel to reduce the risk of selection bias. However, sometimes that is not always feasible, and with a result like 85%+ improvement is not really necessary to do so in order to assume that the control was beaten.
For instance, they could know the average number of cancellations in a week, and see how that number has dropped.
I think this would work out, provided it doesn't matter too much whether the two actions they've taken (the two emails) occur right when the gym signs up or later on.
You're right that an average time to cancel of 61 days implies some may cancel at, say, 80 days. But some gym signed up 20 days before this cohort analysis began, and could have been the one to cancel had it not been for these changes.
Assuming a normal distribution (probably not that accurate, but it's just a guess), the final cancellation rate would be about double that measured until now.
Am I missing something here?